We hired a pro to take photos at our resort, and they turned out lovely. She does not do in park photos, although she did take secret long distance shots of a client proposing, which he gave to his bride on their wedding day! I thought that was cool. It was near the castle, so I guess she made an exception, since it was a slightly different situation, and it probably wasn't obvious what she was doing.
We aren't really rule breakers ourselves, but I think our photographer would do park photos, but didn't feel like she could get away with it. She felt like she would quickly be recognized, after a few sessions. I know she took engagement photos of her best friend in the parks, but didn't charge her.